Abstract
Annulated thienopyrimidine derivatives attracted big interest of the scientific community due to their broad spectrum of biological activities among which are the inhibition of phosphodiesterase, antiproliferative and antimicrobial activities. As a continuation of our studies on the synthesis and biological activity of fused thieno[3,2-d]pyrimidine derivatives, the goal of this paper is the synthesis and study of the properties of compounds containing different heterocycles such as fused thieno[2,3-b]pyridine and tetrazolo[1,5-c]pyrimidine in the same molecule. Thus, starting from the ethyl 1-amino-5-isopropyl-8,8-dimethyl-8,9-dihydro-6H-pyrano[4,3-d]thieno[2,3-b]pyridine-2-carboxylate 1, efficient methods for obtaining new 8-amino-5-isopropyl-2,2-dimethyl-10-(methylthio)-1,4-dihydro-2H-pyrano[4'',3'':4',5']pyrido[3',2':4,5]thieno[3,2-d]pyrimidines 6 and thieno[2,3-e]tetrazolo[1,5-c]pyrimidine 8 are described. The spectroscopic results showed that compound 8 in the solid state is exclusively in the tetrazolo tautomeric form, while in solution an azide-tetrazole equilibrium is present 8A/T. The possible antimicrobial activity of newly synthesized compounds against some gram-positive and gram-negative bacilli strains has been evaluated. The biological tests evidenced that some of them showed promising antimicrobial activity. Two compounds showed similar activity to the one of the used reference drug. The study of structure-activity relationships revealed that the activity of a compound depends mostly on the nature of substituent R1R2. According to the predicted docking studies our compounds could be DnaG inhibitors.
Highlights
During human history man was fighting against a variety of microorganisms that cause infections and diseases, some of them like swine appeared in the form of a pandemic
In continuation of our studies on the synthesis and biological activity of amino derivatives of fused thieno[3,2-d]pyrimidines (Sirakanyan et al 2014, 2016a), in this article we report the synthesis and antimicrobial activity of new 8-amino-5-isopropyl2,2-dimethyl-10-(methylthio)-1,4-dihydro-2Hpyrano[4’’,3’’:4’,5’]pyrido[3’,2’:4,5]thieno[3,2-d] pyrimidines
In a previous paper from us (Sirakanyan et al 2016b) we have described the synthesis of thieno[2,3-e]tetrazolo[1,5-c]pyrimidines, the structure of which was determined by the X-ray crystallography, showing that thieno[2,3-e]
Summary
During human history man was fighting against a variety of microorganisms that cause infections and diseases, some of them like swine appeared in the form of a pandemic. Despite the fact that antimicrobial agents play positive role during the 20th century in the treatment of infectious diseases, the problem of microbial resistance became global, bacteria became resistant to cheap and effective drugs, contributing mostly to human diseases. From another hand the economic crisis, high cost of industrialized medicines, inefficient public access to medical and pharmaceutical care enhanced the rate of infectious disease, becoming a big problem with increasing importance in hospitalized patients, in immuno suppressed patients with AIDS or undergoing cancer therapy and organ transplants
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